Premium
Acetylenic Tetrathiafulvalene Scaffolds – Intramolecular Charge‐Transfer Molecules
Author(s) -
Lincke Kasper,
Christensen Mikkel Andreas,
Diederich François,
Nielsen Mogens Brøndsted
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100291
Subject(s) - chemistry , sonogashira coupling , tetrathiafulvalene , intramolecular force , chromophore , acceptor , photochemistry , molecule , electron acceptor , solubility , iodide , redox , polymer chemistry , stereochemistry , organic chemistry , palladium , catalysis , physics , condensed matter physics
Two tetrathiafulvalene‐functionalized acetylenic scaffolds were synthesized by GlaserHay and Sonogashira coupling reactions; the one scaffold was based on a central dehydroannulene core and the other on a tetraethynylethene core. Peripheral propyl groups on the tetrathiafulvalenes ascertained solubility. The compounds are strong donoracceptor chromophores and exhibit characteristic charge‐transfer absorptions according to UV/VIS absorption spectroscopy. Furthermore, the redox properties were investigated by cyclic and differential‐pulse voltammetries. The experiments allow for a direct comparison between the acceptor strengths of the two acetylenic cores, and the conclusions are supported by electron‐affinity calculations.